The left-back joined Liverpool’s academy in 2003, but two years later he was released.
The Englishman then moved to Tranmere Rovers and after showing his quality for their first team, he was snapped up by Ipswich Town.
Cresswell continued to play well for Ipswich and earned a move to Premier League side West Ham in the summer of 2014.
The 25-year-old is now considered by many as one of the better left-backs in the top flight of English football.
Cresswell has revealed that he always had faith in himself despite being released by Liverpool back in 2005.
“I found it very difficult to deal with - it was devastating," Cresswell told FourFourTwo magazine.
"When you’re that age, you just want to enjoy your football; you don’t see it as something you’re going to do as a job for the rest of your life.
"When I told my dad I’d been let go, he said,’It’s not the end of the world’ - but it was to me.
"To help me recover my confidence he encouraged me to get out there and carry on playing, so the next day I was out in the streets playing football with my mates, really enjoying the game again.
"I never stopped believing in myself. I know I had to keep going. The main thing I focused on was enjoyment and working hard."
Cresswell was West Ham’s best player last season, scoring two goals and creating 34 chances in 38 Premier League matches.
The Englishman had a pass accuracy of 73% and a shot accuracy of 53%, and won 52 headers, 17 dribbles and 31 tackles.
In four Premier League matches this season, Cresswell has created seven chances, has a pass accuracy of 79% and a shot accuracy of 50%, and has won nine headers, four dribbles and two tackles.